Natural and synthetic flavonoid derivatives as new potential tyrosinase inhibitors: a systematic review

Abstract

This review revealed that among all the natural and synthetic flavonoids, the inhibitory findings suggest that the flavonol moiety can serve as an effective and a lead structural scaffold for the further development of novel TIs.

Metabolomic Profile and Biological Properties of Sea Lavender (Limonium algarvense Erben) Plants Cultivated with Aquaculture Wastewaters: Implications for Its Use in Herbal Formulations and Food Additives

“…Some synthetic inhibitors are based on natural flavonoid skeletons providing an effective scaffold for the development of novel tyrosinase inhibitors. For example, flavonoids containing a keto group (e.g., kaempferol and quercetin) are described to have potent tyrosinase inhibition due to their capacity to chelate cooper in the enzyme active site [ 70 ]. In this sense, the higher tyrosinase inhibition found in flower extracts irrigated with 300 mM NaCl may be related with the high abundance of flavonoid-containing keto groups in this extract, such as dihydrokaempferol, naringenin, apigenin, and some of their derivatives.…”

Taxifolin as a Promising Ingredient of Cosmetics for Adult Skin

“…Flavonoids likely exhibit their antioxidant effect through the inhibition of tyrosinasecatalyzed oxidation of L-dihydroxyphenylalanine (L-DOPA) and scavenging of free radicals [13]. Flavonoids are known for their anti-inflammatory [14], anticancer, antimicrobial, antiviral, anti-angiogenic, anti-malarial, neuroprotective, anti-allergic, and antiproliferative activity [15].…”

Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol

“…Mainly three tyrosinase family enzymes are involved in the regulation of melanogenesis in mammalians such as tyrosinase and two tyrosinase-related proteins, TYRP1 and TYRP2. Among these, tyrosinase (EC.1.14.18.1) is the main rate-limiting enzyme that controls the biosynthesis of melanin production by the conversion of L-tyrosine to dopaquinone via L-dopa using monophenolase and diphenolase activities [6][7][8][9]. However, an excess secretion of melanin from melanocytes due to prolonged exposure to sunlight leads to dermatologic disorders such as melasma [10], freckles [11], post-inflammatory melanoderma [12], solar lentigines [13], vitiligo [14], and even cancer [15].…”

“…Hz, 1H),6.93 (d, J = 8.3 Hz, 1H),6.82 (dd, J = 5.3, 1.5 Hz, 1H), 6.50 (d, J = 0.7 Hz, 1H), 4.97 (t, J = 5.6 Hz, 1H), 4.56 (d, J = 5.8 Hz, 3H), 3.92 (d, J = 1.4 Hz, 6H);13 C NMR (CDCl 3, 100 MHz) δ 159.0, 149.8, 149.7, 149.2, 148.6, 137.9, 132.9, 131.8, 128.8, 119.4, 112.0, 111.4, 109.9, 104.4, 56.0, 56.0, 45.7; HRMS m/z [M + H] + calculated for C 20 H 19 ClN 2 O 2 : 355.1208; Found: 355.1219. J = 9.4 Hz, 1H), 6.81 (dd, J = 5.3, 1.5 Hz, 1H), 6.52 (d, J = 0.6 Hz, 1H), 5.06 (t, J = 6.0 Hz, 1H), 4.68 (d, J = 6.2 Hz, 2H), 3.92 (d, J = 2.3 Hz, 6H); 13 C NMR (CDCl 3, 100 MHz) δ 159.0, 149.8, 149.7, 149.2, 148.6, 136.6, 133.4, 131.8, 129.6, 129.3, 128.5, 127.0, 119.5, 111.9, 111.4, 110.0, 104.3, 56.0, 56.0, 44.0; HRMS m/z [M + H] + calculated for C 20 H 19 ClN 2 O 2 : 355.1208; Found: 355.…”

“…Hz, 1H),6.91 (d, J = 8.4 Hz, 1H),6.83 (dd, J = 5.3, 1.5 Hz, 1H), 6.47 (d, J = 0.8 Hz, 1H), 5.08 (t, J = 6.1 Hz, 1H), 4.80 (d, J = 6.2 Hz, 2H), 3.91 (d, J = 2.5 Hz, 6H);13 C NMR (CDCl 3 , 100 MHz) δ 155.0, 145.9, 145.8, 145.3, 144.7, 134.2, 128.3, 127.7, 125.1, 124.1, 123.2, 122.1, 122.0, 115.4, 108.0, 107.4, 105.9, 100.0, 52.0, 51.9, 38.7; HRMS m/z [M + H] + calculated for C 21 H 19 F 3 N 2 O 2 : 389.1472; Found: 389.1484.…”